Methyl morpholine oxide → HCID 66927598, compound

HRID 929750Notes

Reaction equation

HRID 929750 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1)[O:8]2.C[N+]1([O-])CC[O:29]CC1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O=[Os](=O)(=O)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH2:5][C:6](=[O:29])[CH:7]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1)[O:8]2

Participants

6

Reactant 3

HCID 82029Methyl morpholine oxideHCID 656671Sodium PyrosulfiteHCID 23270450HCID 23270450, compound

Product 1

HCID 66927598HCID 66927598, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(2R)-3-[(2R,3S)-5,7,3′,4′-tetrakis(methyloxy)-3-hydroxyflavan)]-5,7,3′,4′-tetramethoxyflavan-3-ene (6) (20 mg, 0.030 mmol) was dissolved in THF (5 mL) and OsO4 (0.9 mg, 0.004 mmol) and N-methylmorpholine-N-oxide (16.3 mg, 0.139 mmol) was added. The reaction mixture is stirred 1-2 days at r.t. under argon (TLC monitoring of consumption of starting material). Solution of sodium metabisulfite (10% aq.) was added and reaction mixture was stirred for 30 minutes. Then was made the extraction 3× with dichloromethane, washed with NaHCO3 (sat. aq.), NaCl (sat. aq.) and dried over MgSO4. Evaporation left crude material which was purified on preparative TLC plates (toluene acetone 6:4) to afford (2S,3S)-3-[(2R,3S)-5,7,3′,4′-tetrakis(methyloxy)-3-hydroxyflavan)]-5,7,3′,4′-tetramethoxyflavan-3-one (7) (Rf 0.19, 6 mg, 0.009 mmol, 30%).

Workup

  1. customreaction mixture
  2. stirringwas stirred for 30 minutes
  3. extractionthe extraction 3× with dichloromethane
  4. washwashed with NaHCO3 (sat. aq.), NaCl (sat. aq.)
  5. dry with materialdried over MgSO4
  6. customEvaporation
  7. waitleft crude material which
  8. customwas purified on preparative TLC plates (toluene acetone 6:4)

Sources & evidence

ORD record
ord-b675b05df0cb4c528318d8a8d04dcf15
Source dataset
uspto-grants-2016_03
Patent number
US09296717B2

Reaction notes

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